Obsessed w/tracking AND Cannot get enough calories

For me it's all about the planning ahead.

If I plot out my days food ahead of time then I can relax on the logging because I can see I'll be at or under my calorie allotment for the day.

For example if you look at my diary for today you'll see it's already filled in so I can "pace" my eating. I eat small snacks throughout the day almost constantly as I'm much happier to graze than have "meals".

I consider myself pretty obsessed by tracking my food so I understand that issue. I don't have a problem getting to my calorie goal, I enjoy eating too much and with my calories pre-logged I know I won't go over so long as I only eat what I've pre-logged.

I also track early, but that's probably a good thing for when you undereat. You can see you're short x calories, so add y and z as a snack or with dinner, etc. As for how to add calories, it's easier than you think. Add a serving of nuts, a spoonful of peanut butter, cook with olive oil, add an avocado to a salad or on top of scrambled eggs in the morning. Or hell, have a piece of good dark chocolate or a serving of ice cream. Too many people try to eat "healthy" and they get horribly restrictive with their diet. You don't have to cut out everything just because "oh it's high fat" or "that's unhealthy". You can have those things, just make sure it's in moderation and fits in your calorie goals.

This is a great post:
http://www.myfitnesspal.com/topics/show/925464-fitting-it-in-giggity

Planning is a big part, but it sounds like you are doing that already. The way I read this is that you plan all your meals for the next day, but still fluctuate greatly. Are the foods you are planning for the next day not the ones you feel like eating when it comes time? Perhaps rather than planning strict meals which you will eat no matter what, have an idea of how many calories you plan to eat for breakfast, lunch, dinner, snacks, etc.. Then have a half dozen meal ideas that you can decide between when you are ready to eat.

I guess if you are already tracking and not hitting goals, find out why you are having the discrepancies in calories.

It can be a bit dangerous to be overly obsessed with tracking your calories. So if you feel like it's really impacting on your mental state to be tracking them or something then it's best to try to stop or see someone about it.

If you're hungry then eat (sensibly). If you're not hungry then don't.
Learn what foods keep you satisfied with enough energy for the day without your body getting bloated. Don't feel like you need to meet your calorie goals every day - if you're sitting at your desk trying to eat more to meet your calorie goals while you're already full, then stop, because if you're full you don't need to eat more.

It's also about more than just the calories, look at the nutritional info and make sure you're getting enough of everything else - like protein, calcium, vitamins etc and make sure you aren't eating too much sugar. Too much sugar can make you feel hungrier and also contains a lot of calories, while protein makes you feel fuller for longer AND helps maintain muscle mass - which is vital for staying healthy. Calorie restriction can cause your body to freak out and break down muscle, to help this stop happening you need to feed your muscles protein.
It's not just all about calories. In the grand scheme of things, they end up being a pimple on a pumpkin.
Hope this has helped! (: